Global InformationLysine acetylsalicylate information
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| Formula | C15H22N2O6 |
| Molar mass | 326.349 g·mol−1 |
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Lysine acetylsalicylate, also known as aspirin DL-lysine or lysine aspirin, is a more soluble form of acetylsalicylic acid (aspirin). As with aspirin itself, it is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic, anti-inflammatory, antithrombotic and antipyretic properties.[1] It is composed of the ammonium form of the amino acid lysine paired with the conjugate base of aspirin.
Lysine acetylsalicylate was developed for intravenous administration in acute pain management, enabling faster onset of action compared to oral aspirin.[2] Adverse effects are similar to those of orally administered aspirin, including upset stomach, and heartburn.[3] In more serious cases, it can cause peptic ulcers, gastric bleeding, and exacerbate asthma. Due to its antithrombotic properties, patients using lysine acetylsalicylate or oral aspirin have an increased risk of bleeding especially for patients on blood thinning medications. It should not be used in children with infections, as it poses a risk of Reye syndrome, nor should it be used in the final trimester of pregnancy due to risks of premature closure of the foramen ovale in the fetal heart.
The therapeutic effects of salicylic acids were first documented in 1763 by Edward Stone, with acetylsalicylic acid being synthesized by Felix Hoffmann, a chemist working under Bayer, in 1897.[4] Acetylsalicylic acid-derived salt compounds were first discovered in 1970,[5] and the synthesis of lysine acetylsalicylate was first documented in 1978.[6]
- ^ "Lysine acetylsalicylate". go.drugbank.com. Retrieved 2023-03-14.
- ^ "Lysine Acetylsalicylate - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 2023-03-14.
- ^ Abramson SB (2021-04-21). Furst DE, Seo P (eds.). "Aspirin: mechanism of action, major toxicities, and use in rheumatic diseases". UptoDate. Waltham (MA): Wolters Kluwer N.V. Retrieved 2023-03-14.
- ^ Montinari MR, Minelli S, De Caterina R (February 2019). "The first 3500 years of aspirin history from its roots - A concise summary". Vascular Pharmacology. 113: 1–8. doi:10.1016/j.vph.2018.10.008. PMID 30391545. S2CID 53215011.
- ^ DE 2156806, "Arginine acetylsalicylates, processes for their production and pharmaceutical preparations containing them", issued 28 April 1983, assigned to METABIO, Boulogne (Frankreich).
- ^ ES 456529A1, "Procedure for preparing lycine acetilsalicilate.", issued 1 February 1978, assigned to Egyb SA.